BRPI0809193A2 - Compostos orgânicos e seus usos - Google Patents
Compostos orgânicos e seus usos Download PDFInfo
- Publication number
- BRPI0809193A2 BRPI0809193A2 BRPI0809193-5A BRPI0809193A BRPI0809193A2 BR PI0809193 A2 BRPI0809193 A2 BR PI0809193A2 BR PI0809193 A BRPI0809193 A BR PI0809193A BR PI0809193 A2 BRPI0809193 A2 BR PI0809193A2
- Authority
- BR
- Brazil
- Prior art keywords
- piperazin
- benzyl
- phthalazin
- pyridin
- phthalazine
- Prior art date
Links
- 150000002894 organic compounds Chemical class 0.000 title description 17
- 150000001875 compounds Chemical class 0.000 claims description 284
- -1 -OH Chemical group 0.000 claims description 121
- 238000000034 method Methods 0.000 claims description 62
- 125000000217 alkyl group Chemical group 0.000 claims description 50
- 125000003118 aryl group Chemical group 0.000 claims description 47
- 230000037361 pathway Effects 0.000 claims description 37
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 26
- 238000011282 treatment Methods 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 241000124008 Mammalia Species 0.000 claims description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 7
- 125000002950 monocyclic group Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 claims description 6
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000002619 bicyclic group Chemical group 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical group C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- QSMQHCAGPSMYSK-UHFFFAOYSA-N 4-[4-[6-[(4-fluorophenyl)methyl]-5-methylpyridazin-3-yl]piperazin-1-yl]benzonitrile Chemical compound CC1=CC(N2CCN(CC2)C=2C=CC(=CC=2)C#N)=NN=C1CC1=CC=C(F)C=C1 QSMQHCAGPSMYSK-UHFFFAOYSA-N 0.000 claims description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Chemical group C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- NREWZBJDYHPYAU-UHFFFAOYSA-N 1-(4-naphthalen-2-ylpiperazin-1-yl)-4-(pyridin-4-ylmethyl)phthalazine Chemical compound N=1N=C(N2CCN(CC2)C=2C=C3C=CC=CC3=CC=2)C2=CC=CC=C2C=1CC1=CC=NC=C1 NREWZBJDYHPYAU-UHFFFAOYSA-N 0.000 claims 1
- XSHIMNJHGMKCSB-UHFFFAOYSA-N 1-(4-phenylpiperidin-1-yl)-4-(pyridin-4-ylmethyl)phthalazine Chemical compound N=1N=C(N2CCC(CC2)C=2C=CC=CC=2)C2=CC=CC=C2C=1CC1=CC=NC=C1 XSHIMNJHGMKCSB-UHFFFAOYSA-N 0.000 claims 1
- HVCKRXNCZNJASA-UHFFFAOYSA-N 1-(pyridin-4-ylmethyl)-4-(4-pyridin-2-ylpiperazin-1-yl)phthalazine Chemical compound N=1N=C(N2CCN(CC2)C=2N=CC=CC=2)C2=CC=CC=C2C=1CC1=CC=NC=C1 HVCKRXNCZNJASA-UHFFFAOYSA-N 0.000 claims 1
- TZAASNNFIRTGOY-UHFFFAOYSA-N 1-(pyridin-4-ylmethyl)-4-(4-pyridin-4-ylpiperazin-1-yl)phthalazine Chemical compound N=1N=C(N2CCN(CC2)C=2C=CN=CC=2)C2=CC=CC=C2C=1CC1=CC=NC=C1 TZAASNNFIRTGOY-UHFFFAOYSA-N 0.000 claims 1
- PBGGTBCALLLFEL-UHFFFAOYSA-N 1-(pyridin-4-ylmethyl)-4-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]phthalazine Chemical compound FC(F)(F)C1=CC=CC(N2CCN(CC2)C=2C3=CC=CC=C3C(CC=3C=CN=CC=3)=NN=2)=C1 PBGGTBCALLLFEL-UHFFFAOYSA-N 0.000 claims 1
- HCGUHZNRAWNJJF-UHFFFAOYSA-N 1-[(2-methylpyridin-4-yl)methyl]-4-(4-naphthalen-1-ylpiperazin-1-yl)phthalazine Chemical compound C1=NC(C)=CC(CC=2C3=CC=CC=C3C(N3CCN(CC3)C=3C4=CC=CC=C4C=CC=3)=NN=2)=C1 HCGUHZNRAWNJJF-UHFFFAOYSA-N 0.000 claims 1
- MEKLHRVELUHMFI-UHFFFAOYSA-N 1-[(2-methylpyridin-4-yl)methyl]-4-(4-naphthalen-2-ylpiperazin-1-yl)phthalazine Chemical compound C1=NC(C)=CC(CC=2C3=CC=CC=C3C(N3CCN(CC3)C=3C=C4C=CC=CC4=CC=3)=NN=2)=C1 MEKLHRVELUHMFI-UHFFFAOYSA-N 0.000 claims 1
- YOHXGDGZLIZYMM-UHFFFAOYSA-N 1-[(2-methylpyridin-4-yl)methyl]-4-(4-phenylpiperazin-1-yl)phthalazine Chemical compound C1=NC(C)=CC(CC=2C3=CC=CC=C3C(N3CCN(CC3)C=3C=CC=CC=3)=NN=2)=C1 YOHXGDGZLIZYMM-UHFFFAOYSA-N 0.000 claims 1
- PYIMKFNVGGYUFB-UHFFFAOYSA-N 1-[(2-methylpyridin-4-yl)methyl]-4-(4-phenylpiperidin-1-yl)phthalazine Chemical compound C1=NC(C)=CC(CC=2C3=CC=CC=C3C(N3CCC(CC3)C=3C=CC=CC=3)=NN=2)=C1 PYIMKFNVGGYUFB-UHFFFAOYSA-N 0.000 claims 1
- QNCOLCVCRUCSKS-UHFFFAOYSA-N 1-[(2-methylpyridin-4-yl)methyl]-4-(4-pyridin-2-ylpiperazin-1-yl)phthalazine Chemical compound C1=NC(C)=CC(CC=2C3=CC=CC=C3C(N3CCN(CC3)C=3N=CC=CC=3)=NN=2)=C1 QNCOLCVCRUCSKS-UHFFFAOYSA-N 0.000 claims 1
- DYKHGEUMVJEKLB-UHFFFAOYSA-N 1-[(4-fluorophenyl)methyl]-3-[1-[5-(trifluoromethyl)pyridin-2-yl]piperidin-4-yl]indole Chemical group C1=CC(F)=CC=C1CN1C2=CC=CC=C2C(C2CCN(CC2)C=2N=CC(=CC=2)C(F)(F)F)=C1 DYKHGEUMVJEKLB-UHFFFAOYSA-N 0.000 claims 1
- FCVJYRXOVHZILY-UHFFFAOYSA-N 1-[3-methyl-4-(4-methylphenyl)piperazin-1-yl]-4-(pyridin-4-ylmethyl)phthalazine Chemical compound CC1CN(C=2C3=CC=CC=C3C(CC=3C=CN=CC=3)=NN=2)CCN1C1=CC=C(C)C=C1 FCVJYRXOVHZILY-UHFFFAOYSA-N 0.000 claims 1
- KOXVHTNAKPJMBU-UHFFFAOYSA-N 1-[3-methyl-4-(4-methylphenyl)piperazin-1-yl]-4-[(2-methylpyridin-4-yl)methyl]phthalazine Chemical compound CC1CN(C=2C3=CC=CC=C3C(CC=3C=C(C)N=CC=3)=NN=2)CCN1C1=CC=C(C)C=C1 KOXVHTNAKPJMBU-UHFFFAOYSA-N 0.000 claims 1
- KORCWOUBNUBJEI-UHFFFAOYSA-N 1-[4-(4-tert-butylphenyl)piperazin-1-yl]-4-(pyridin-4-ylmethyl)phthalazine Chemical compound C1=CC(C(C)(C)C)=CC=C1N1CCN(C=2C3=CC=CC=C3C(CC=3C=CN=CC=3)=NN=2)CC1 KORCWOUBNUBJEI-UHFFFAOYSA-N 0.000 claims 1
- YOMAHAPBOWESHU-UHFFFAOYSA-N 1-[4-(4-tert-butylphenyl)piperazin-1-yl]-4-[(3,5-dichlorophenyl)methyl]phthalazine Chemical compound C1=CC(C(C)(C)C)=CC=C1N1CCN(C=2C3=CC=CC=C3C(CC=3C=C(Cl)C=C(Cl)C=3)=NN=2)CC1 YOMAHAPBOWESHU-UHFFFAOYSA-N 0.000 claims 1
- UUAZQBSQYZABEQ-UHFFFAOYSA-N 1-benzyl-4-(4-naphthalen-1-ylpiperazin-1-yl)phthalazine Chemical compound N=1N=C(N2CCN(CC2)C=2C3=CC=CC=C3C=CC=2)C2=CC=CC=C2C=1CC1=CC=CC=C1 UUAZQBSQYZABEQ-UHFFFAOYSA-N 0.000 claims 1
- JJSXUPUQGOZNAD-UHFFFAOYSA-N 1-benzyl-4-(4-phenylpiperidin-1-yl)phthalazine Chemical compound N=1N=C(N2CCC(CC2)C=2C=CC=CC=2)C2=CC=CC=C2C=1CC1=CC=CC=C1 JJSXUPUQGOZNAD-UHFFFAOYSA-N 0.000 claims 1
- FCTUWPXBMWNCFN-UHFFFAOYSA-N 1-benzyl-4-(4-pyridin-2-ylpiperazin-1-yl)phthalazine Chemical compound N=1N=C(N2CCN(CC2)C=2N=CC=CC=2)C2=CC=CC=C2C=1CC1=CC=CC=C1 FCTUWPXBMWNCFN-UHFFFAOYSA-N 0.000 claims 1
- ZOMATTARMBPHPC-UHFFFAOYSA-N 1-benzyl-4-(4-pyridin-4-ylpiperazin-1-yl)phthalazine Chemical compound N=1N=C(N2CCN(CC2)C=2C=CN=CC=2)C2=CC=CC=C2C=1CC1=CC=CC=C1 ZOMATTARMBPHPC-UHFFFAOYSA-N 0.000 claims 1
- CDWQMKHXVNDQPE-UHFFFAOYSA-N 1-benzyl-4-(4-pyrimidin-2-yl-1,4-diazepan-1-yl)phthalazine Chemical compound N=1N=C(N2CCN(CCC2)C=2N=CC=CN=2)C2=CC=CC=C2C=1CC1=CC=CC=C1 CDWQMKHXVNDQPE-UHFFFAOYSA-N 0.000 claims 1
- HMRVINPZCLHMPP-UHFFFAOYSA-N 1-benzyl-4-(4-pyrimidin-2-ylpiperazin-1-yl)phthalazine Chemical compound N=1N=C(N2CCN(CC2)C=2N=CC=CN=2)C2=CC=CC=C2C=1CC1=CC=CC=C1 HMRVINPZCLHMPP-UHFFFAOYSA-N 0.000 claims 1
- LCAPNICGXDVDSP-UHFFFAOYSA-N 1-benzyl-4-(4-quinolin-2-ylpiperazin-1-yl)phthalazine Chemical compound N=1N=C(N2CCN(CC2)C=2N=C3C=CC=CC3=CC=2)C2=CC=CC=C2C=1CC1=CC=CC=C1 LCAPNICGXDVDSP-UHFFFAOYSA-N 0.000 claims 1
- HZNGEWZOSJOMNW-UHFFFAOYSA-N 1-benzyl-4-[3-methyl-4-(4-methylphenyl)piperazin-1-yl]phthalazine Chemical compound CC1CN(C=2C3=CC=CC=C3C(CC=3C=CC=CC=3)=NN=2)CCN1C1=CC=C(C)C=C1 HZNGEWZOSJOMNW-UHFFFAOYSA-N 0.000 claims 1
- PJLVDQFZIOWOLJ-UHFFFAOYSA-N 1-benzyl-4-[4-(2,5-difluoropyridin-3-yl)piperazin-1-yl]phthalazine Chemical compound FC1=CN=C(F)C(N2CCN(CC2)C=2C3=CC=CC=C3C(CC=3C=CC=CC=3)=NN=2)=C1 PJLVDQFZIOWOLJ-UHFFFAOYSA-N 0.000 claims 1
- MHQDYUARUYMKMC-UHFFFAOYSA-N 1-benzyl-4-[4-(3,4-dichlorophenyl)piperazin-1-yl]phthalazine Chemical compound C1=C(Cl)C(Cl)=CC=C1N1CCN(C=2C3=CC=CC=C3C(CC=3C=CC=CC=3)=NN=2)CC1 MHQDYUARUYMKMC-UHFFFAOYSA-N 0.000 claims 1
- ADSXBWXAYYALMU-UHFFFAOYSA-N 1-benzyl-4-[4-(3,5-difluoropyridin-2-yl)piperazin-1-yl]phthalazine Chemical compound FC1=CC(F)=CN=C1N1CCN(C=2C3=CC=CC=C3C(CC=3C=CC=CC=3)=NN=2)CC1 ADSXBWXAYYALMU-UHFFFAOYSA-N 0.000 claims 1
- UDCDFBSCTFIEKM-UHFFFAOYSA-N 1-benzyl-4-[4-(4,6-dimethylpyrimidin-2-yl)piperazin-1-yl]phthalazine Chemical compound CC1=CC(C)=NC(N2CCN(CC2)C=2C3=CC=CC=C3C(CC=3C=CC=CC=3)=NN=2)=N1 UDCDFBSCTFIEKM-UHFFFAOYSA-N 0.000 claims 1
- WPYOMQSSPYPDHR-UHFFFAOYSA-N 1-benzyl-4-[4-(4-methylpyrimidin-2-yl)-1,4-diazepan-1-yl]phthalazine Chemical compound CC1=CC=NC(N2CCN(CCC2)C=2C3=CC=CC=C3C(CC=3C=CC=CC=3)=NN=2)=N1 WPYOMQSSPYPDHR-UHFFFAOYSA-N 0.000 claims 1
- AMXBKTRGEYGPSZ-UHFFFAOYSA-N 1-benzyl-4-[4-(4-tert-butylphenyl)piperazin-1-yl]phthalazine Chemical compound C1=CC(C(C)(C)C)=CC=C1N1CCN(C=2C3=CC=CC=C3C(CC=3C=CC=CC=3)=NN=2)CC1 AMXBKTRGEYGPSZ-UHFFFAOYSA-N 0.000 claims 1
- MRSJUQOXXMRVSG-UHFFFAOYSA-N 1-benzyl-4-[4-(5-chloro-3-fluoropyridin-2-yl)piperazin-1-yl]phthalazine Chemical compound FC1=CC(Cl)=CN=C1N1CCN(C=2C3=CC=CC=C3C(CC=3C=CC=CC=3)=NN=2)CC1 MRSJUQOXXMRVSG-UHFFFAOYSA-N 0.000 claims 1
- APFNDNPQXUAMNK-UHFFFAOYSA-N 1-benzyl-4-[4-(5-ethylpyrimidin-2-yl)-1,4-diazepan-1-yl]phthalazine Chemical compound N1=CC(CC)=CN=C1N1CCN(C=2C3=CC=CC=C3C(CC=3C=CC=CC=3)=NN=2)CCC1 APFNDNPQXUAMNK-UHFFFAOYSA-N 0.000 claims 1
- DMHPFZIEPAKAJH-UHFFFAOYSA-N 1-benzyl-4-[4-(5-ethylpyrimidin-2-yl)piperazin-1-yl]phthalazine Chemical compound N1=CC(CC)=CN=C1N1CCN(C=2C3=CC=CC=C3C(CC=3C=CC=CC=3)=NN=2)CC1 DMHPFZIEPAKAJH-UHFFFAOYSA-N 0.000 claims 1
- HXKBYTPJUYFEDS-UHFFFAOYSA-N 1-benzyl-4-[4-(5-propylpyrimidin-2-yl)-1,4-diazepan-1-yl]phthalazine Chemical compound N1=CC(CCC)=CN=C1N1CCN(C=2C3=CC=CC=C3C(CC=3C=CC=CC=3)=NN=2)CCC1 HXKBYTPJUYFEDS-UHFFFAOYSA-N 0.000 claims 1
- QPYRGBRCKYCHFS-UHFFFAOYSA-N 1-benzyl-4-[4-(5-propylpyrimidin-2-yl)piperazin-1-yl]phthalazine Chemical compound N1=CC(CCC)=CN=C1N1CCN(C=2C3=CC=CC=C3C(CC=3C=CC=CC=3)=NN=2)CC1 QPYRGBRCKYCHFS-UHFFFAOYSA-N 0.000 claims 1
- PEABBNOZODJWCW-UHFFFAOYSA-N 1-benzyl-4-[4-[4-(trifluoromethyl)phenyl]piperazin-1-yl]phthalazine Chemical compound C1=CC(C(F)(F)F)=CC=C1N1CCN(C=2C3=CC=CC=C3C(CC=3C=CC=CC=3)=NN=2)CC1 PEABBNOZODJWCW-UHFFFAOYSA-N 0.000 claims 1
- WIBNSJFMOKMURW-UHFFFAOYSA-N 1-benzyl-4-[4-[4-(trifluoromethyl)pyrimidin-2-yl]piperazin-1-yl]phthalazine Chemical compound FC(F)(F)C1=CC=NC(N2CCN(CC2)C=2C3=CC=CC=C3C(CC=3C=CC=CC=3)=NN=2)=N1 WIBNSJFMOKMURW-UHFFFAOYSA-N 0.000 claims 1
- DESUHVIRYTUYHS-UHFFFAOYSA-N 1-benzyl-4-[4-[5-(trifluoromethyl)pyridin-2-yl]-1,4-diazepan-1-yl]phthalazine Chemical compound N1=CC(C(F)(F)F)=CC=C1N1CCN(C=2C3=CC=CC=C3C(CC=3C=CC=CC=3)=NN=2)CCC1 DESUHVIRYTUYHS-UHFFFAOYSA-N 0.000 claims 1
- NTZIYOUDVSCPRE-UHFFFAOYSA-N 1-benzyl-4-[4-[5-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]phthalazine Chemical compound N1=CC(C(F)(F)F)=CC=C1N1CCN(C=2C3=CC=CC=C3C(CC=3C=CC=CC=3)=NN=2)CC1 NTZIYOUDVSCPRE-UHFFFAOYSA-N 0.000 claims 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- OUTGATYBBGJRSR-UHFFFAOYSA-N 2-[4-(4-benzylphthalazin-1-yl)piperazin-1-yl]-4-methoxy-1h-pyrimidin-6-one Chemical compound COC1=CC(=O)NC(N2CCN(CC2)C=2C3=CC=CC=C3C(CC=3C=CC=CC=3)=NN=2)=N1 OUTGATYBBGJRSR-UHFFFAOYSA-N 0.000 claims 1
- JBWHVUZHQZSBAU-UHFFFAOYSA-N 2-[4-(4-benzylphthalazin-1-yl)piperazin-1-yl]pyrimidine-5-carbonitrile Chemical compound N1=CC(C#N)=CN=C1N1CCN(C=2C3=CC=CC=C3C(CC=3C=CC=CC=3)=NN=2)CC1 JBWHVUZHQZSBAU-UHFFFAOYSA-N 0.000 claims 1
- KSWYJUIFHPSZOL-UHFFFAOYSA-N 2-[6-[4-(4-benzylphthalazin-1-yl)piperazin-1-yl]pyridin-3-yl]propan-2-ol Chemical compound N1=CC(C(C)(O)C)=CC=C1N1CCN(C=2C3=CC=CC=C3C(CC=3C=CC=CC=3)=NN=2)CC1 KSWYJUIFHPSZOL-UHFFFAOYSA-N 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- 125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 1
- ZUOPMEBGUXAHFJ-UHFFFAOYSA-N 3-[4-[1-[(4-fluorophenyl)methyl]indol-3-yl]piperidine-1-carbonyl]benzonitrile Chemical compound C1=CC(F)=CC=C1CN1C2=CC=CC=C2C(C2CCN(CC2)C(=O)C=2C=C(C=CC=2)C#N)=C1 ZUOPMEBGUXAHFJ-UHFFFAOYSA-N 0.000 claims 1
- YKXAENNLNUNCRL-UHFFFAOYSA-N 3-benzyl-4-methyl-6-[4-[5-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]pyridazine Chemical compound CC1=CC(N2CCN(CC2)C=2N=CC(=CC=2)C(F)(F)F)=NN=C1CC1=CC=CC=C1 YKXAENNLNUNCRL-UHFFFAOYSA-N 0.000 claims 1
- CJYHWHOHWHGPIN-UHFFFAOYSA-N 4-[4-(4-benzylphthalazin-1-yl)piperazin-1-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1N1CCN(C=2C3=CC=CC=C3C(CC=3C=CC=CC=3)=NN=2)CC1 CJYHWHOHWHGPIN-UHFFFAOYSA-N 0.000 claims 1
- SDIWFGXIDYJTIS-UHFFFAOYSA-N 4-[4-(4-tert-butylphenyl)piperazin-1-yl]-6-methyl-1-(pyridin-4-ylmethyl)phthalazine Chemical compound N=1N=C(N2CCN(CC2)C=2C=CC(=CC=2)C(C)(C)C)C2=CC(C)=CC=C2C=1CC1=CC=NC=C1 SDIWFGXIDYJTIS-UHFFFAOYSA-N 0.000 claims 1
- HCSXBVOINMRGSU-UHFFFAOYSA-N 4-[4-[6-[(4-chlorophenyl)methyl]-4-methylpyridazin-3-yl]piperazin-1-yl]pyridine-3-carbonitrile Chemical compound N=1N=C(N2CCN(CC2)C=2C(=CN=CC=2)C#N)C(C)=CC=1CC1=CC=C(Cl)C=C1 HCSXBVOINMRGSU-UHFFFAOYSA-N 0.000 claims 1
- SXXNBFSKRFOPMV-UHFFFAOYSA-N 4-[4-[6-[(4-chlorophenyl)methyl]-5-methylpyridazin-3-yl]piperazin-1-yl]pyridine-3-carbonitrile Chemical compound CC1=CC(N2CCN(CC2)C=2C(=CN=CC=2)C#N)=NN=C1CC1=CC=C(Cl)C=C1 SXXNBFSKRFOPMV-UHFFFAOYSA-N 0.000 claims 1
- OWGWZSMXQAXZDR-UHFFFAOYSA-N 4-[4-[6-[(4-fluorophenyl)methyl]-4,5-dimethylpyridazin-3-yl]piperazin-1-yl]pyridine-3-carbonitrile Chemical compound CC1=C(C)C(N2CCN(CC2)C=2C(=CN=CC=2)C#N)=NN=C1CC1=CC=C(F)C=C1 OWGWZSMXQAXZDR-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
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- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
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